


If the Diciannoveventitre Derby Shoe Fits—

by PaperAnn



Series: PaperAnn's Kink Bingo 2017 Works [16]
Category: Supernatural
Genre: Alpha Sam, Alpha/Beta/Omega Dynamics, Alternate Universe, Anal Fingering, Awkward Sexual Situations, Blow Jobs, Humor, Knotting, M/M, Office Sex, Omega Dean, Shameless Smut, Shoe Kink, Supernatural Kink Bingo 2017, Unrelated Dean Winchester/Sam Winchester
Language: English
Status: Completed
Published: 2017-10-23
Updated: 2017-10-23
Packaged: 2019-01-22 02:05:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,555
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12471052
Author URL: https://archiveofourown.org/users/PaperAnn/pseuds/PaperAnn
Summary: A previous awkward interaction between Dean Smith and Sam Wesson leaves them with a silent elevator trip and Dean’s roaming eyes.  When he shockingly discovers that Mr. Creepy-Tech-Support is wearing a pair of shoes he’s been fawning over, needing in his closet since the moment he saw those beauties, it leads to something impossiblymoreawkward.Sam scents desire and assumes it’s Dean wantinghim, except it’s really Dean wanting hisshoes.  Well, it’s a good thing Dean finds this guy attractive and he doesn't discriminate.  Plus, his office is only the press of a button away...





	If the Diciannoveventitre Derby Shoe Fits—

**Author's Note:**

> Written for SPN Kink Bingo 2017  
> Square Filled: Shoe Kink

When it came to awkward situations, Dean Smith tended to face them head on.

He didn’t climb the corporate ladder by letting people walk all over him.  He was assertive, he was direct, and he knew what he wanted.  Dean _had to._   He went into business with the goal of getting the best position Sandover had to offer (without flying too close to the sun, Young Icarus) and he was going all-in as an omega.  That meant unwavering confidence.

Well, in most situations.

This elevator thing?  Was a whole new issue.

This guy, he was tech support, Dean knew from his yellow shirt plus a whiff of the stale coffee and sweat from crammed quarters inside the cubicles.  He didn’t seem to appreciate Dean’s need for personal space!  At first, it wasn’t a problem because this guy was hot.  Totally Dean’s type, but the second the dude asked a straight-up bizarre question, that flew out the window.

Of course, the sexiest guy who worked at Sandover would be a nut job.  Now he had to ignore him and stew in silence.  Great.

After Dean shut him down, his gaze fell to the floor and his mouth fell open because…

Not only was this dude gorgeous (ignoring the coo-coo thing), he was wearing a pair of Diciannoveventitres!

But how the hell could someone in _tech support_ afford to buy these babies?!  This pair alone was over two and a half grand!  Dean had been bartering with himself, on the fence over and over because, goddammit, he _needed_ these in his closest!  And the creepy hottie was sporting them at work!  
  
This.  Exact.  Friggin.  Pair!  The damn Derby Shoes!

Dean was enchanted, seeing them in real life and close up, rather than on a webpage or the one time he’d actually tried a version of them on at a high-end store, only to remorsefully put them back.  They had fit like a dream, but he justified sending them back because they didn’t have his color.  Of course, the distressed tan was a classic, Dean would have taken it in a heartbeat, but the ones on this guys feet?  
  
The real _Classic Derbies?_ In black horse leather?  
  
Dean just...didn’t have the words.  Of course, he wasn’t one to condone animal abuse, but there was something special about these shoes he’d always been drawn to.  The elegance of the formal shape, matched with the rough-and-tumble finish and the grey laces.  The stacked heel made the fit that much more sleek, but he didn’t understand why this giant needed anymore height on him!  
  
Then, other questions filled his head, like what if he spilled food on them?  That wreck of a human-kennel where he worked was the last place he’d subject these beauties, these masterpieces to and—!

“Uh, Mr. Smith?” his voice was as little shaky, and Dean’s attention jolted back upward to face Wesson, completely forgetting there was a human attached to those perfect shoes.

He noticed they were alone and they were on their floor, so Dean cleared his throat and marched out into the parking garage, saying, “Oh, sorry.  Just…long day.”

Just when he thought he was in the clear, a hand gripped his shoulder (albeit gently) but it caused Dean to whip around like he was being assaulted.  What could he say?  Omega instincts and self-preservation in the face of an alpha kicked in like a bad habit.

“What the hell—?!”

“Sam,” he supplied, and there was an out of place smile on his face.  “Sorry, you weren’t responding, or hearing me, I…”  The faint blush on his cheeks was adorable, Dean would give him that.  “Your scent.  What’s, uh.  Well, what provoked that?”

Dean tilted his head to the side, because he had no idea what the hell he was talking about.  “Excuse me?  What about my scent?”

Sam took a step in, and hot damn, _his_ scent was heady and it was drawing Dean in at an alarming pace.  This wasn’t good.  That, and the look of barely contained lust in his eyes?  Fuck, fuck, fuck!

“Your scent, it was like you wanted something.  And you wanted it now.”  The alpha dared to reach out and grab Dean’s hip, bringing them closer.  “Since we were the only people in that elevator, I can only make the assumption…”

Shit!  Dean had royally fucked this up, because he couldn’t exactly tell this gorgeous, aroused and heavenly-scented alpha that _he_ wasn’t the one he wanted.  

Dean wanted his fucking shoes.  That was where his ‘need’ stemmed from, not…

No, Dean decided he couldn’t leave him hanging, because now that Sam had transformed in front of him like this?  The creepy weirdo part was in the past.

Sam was fifty shades of sexy and enticing, Dean’s body was naturally responding, and maybe now there was something else that he wanted too...  He was being pulled closer not even realizing he’d dropped his briefcase until it was on the ground.  The omega didn’t know what was going on…but that Looney Tunes thing that lingered?

Okay, he needed to get that out of the way.  No way in hell he was falling for Norman Bates!

Even as Sam grabbed the base of Dean’s skull to pull them together, and yeah—Dean totally moaned by the way this alpha was _taking,_ it shot directly south—

“Hold on a second,” Dean planted his hands on Sam’s chest and, holy shit, the muscles under that poor excuse for a polo?  He was pure strength, steel, and Dean totally copped a feel before he asked, “That freaky ’do we know each other?’  Was that a pick-up line, or are you—”

“Heh, you’re trying to figure out if I’m crazy.”  Sam exhaled sharply, his gaze flickering between Dean’s eyes and his lips.  “I’m sorry, I thought you were someone else, but you weren’t."  With an eyebrow raised, Sam dared to say, "You can’t think I’m _that_ crazy if that’s slick I already smell…”

Sam looked haughty: he was bold, he was brazen and, dammit, he was right!

Dean started pushing.  Quite literally.  He started pushing Sam backwards, who looked confused (more and more by the second) until his back slammed against the hard, cold and shut elevator doors.  The omega reached out and pressed the ascending arrow.

“What are you—” Sam was cut off by Dean’s hot mouth on his, and then he couldn’t speak.

Sam didn't mind the way Dean shut him up, he hauled the omega as close as their bodies could press against each other, their erections rutting together and gasps being forced from their chests.  When the door dinged announcing the elevator arrived on their floor, Dean recoiled.  He gave them both enough space and took a second to thoroughly enjoy the debauched and stunned alpha in front of him.

Luckily, when he looked over Sam’s shoulder they were still alone.  Dean shoved the flabbergasted man into the elevator and punched in a button.

The alpha was still confused as hell, and the omega's grin turned wicked.  When Dean’s hand dove down the front of Sam’s pants, he knew he had him wrapped around his finger - Sam sputtering in surprise and breathless.  Dean also took a moment to appreciate those damn shoes.  If he didn’t have a cock in his hand, if he wasn’t imagining the thickness and the beautiful disaster it would wreck on his body, he’d ask him once and for all if they were the real deal or knock offs—  
  
But Dean did, indeed, have his hand wrapped around one hell of an erection.  As he looked forward to the main event, he was getting slicker and weak-kneed by the second.

Sam was grabbing at the handrails and arching into Dean’s touch, a smirk spreading across Dean’s face when he explained, “Yeah, Sam.  That is slick you scent.  You’re too damn tempting.  There’s no way either of us are gonna keep our hands to ourselves and make it to a bed in time before we tear each other apart.”  He pulled his hand out of the alpha’s pants and with a mischievous grin, and divulged, “Luckily, I’ve got _quite_ the roomy, private office.”

It looked like Sam was about to choke on his own tongue.  “Are you saying you want me to bend you over your desk and fuck you raw in _your office_?  While there are still people milling around, putting in overtime?”

“That’s exactly what I’m saying,” Dean practically purred, trying to fix Sam’s hair.  Soon, they’d arrived on the floor and he couldn't mosey around looking like this.  “Now, pull yourself together for the walk, and then we’ll get to the good stuff.”

Instantly, Sam was poised and ready, like nothing had happened.  Dean was almost offended, because he thought he’d done a pretty damn good job of ruining his fortitude beforehand, but Sam…wow.  He was just full of surprises.  At least it made the pre-walk of shame easy enough, so long as no one caught a whiff of their scent.

That would have been the giveaway, it was soaked into their clothing, hell, it was leaking between Dean’s legs as they spoke.

Just as they thought they were in the clear, and Dean had the key to his office out and prepared, his assistant turned the corner with her jacket on.

“Mr. Smith!  I thought you’d already left!”  Lisa abruptly began to pull her coat off, fumbling, “I apologize, what do you need from me?  I know we’re reaching deadlines, I’ll be happy to stay, but…” she paused and tilted her head, “Who’s that?”

“Miss Braeden, you’re free to go home, this is Sam, we’re having a meeting.  It’s nothing you need to worry about.”  Dean smiled and hoped his voice came out as soothing and believable, because Lisa needed to get the fuck out of there, right now!

And, of course, she was wary, “Are you sure you don’t want me to wait and type up the minutes?  Make a log or—”

“Lisa.”  Dean’s voice was firm when he urged, “I promise.  Get home to Ben, I’m sure he’d love a good supper with his mother.”

That, right there, was the key word.  She gave in, even though she deliberately scented the air and whatever she smelled?   _That_ got her moving even faster.  In fact, she blurted out, “I’ll see you in the morning De—Mr. Smith.  Enjoy your night!” and hustled ass out of there.

Yeah, the omega had a feeling that she knew precisely what was happening, no matter how good their game faces.  Still, as Dean unlocked the door, he thought about how Lisa was on his side, so it didn’t matter.  He let them both inside, locked the door behind them, and as to not draw attention only turned on his desk lamp.  All the blinds were already closed, so it truly was private, thank God!

When Dean looked over his shoulder, that calm, composed version of Sam strutting through the field of their coworkers?  

He’d vanished.  The alpha in front of Dean seized the opportunity to haul their lips together again, to manhandle Dean on top of his desk and to suck the air from his lungs.  Dean grappled at Sam’s back and wrapped his legs around his hips, but that wasn’t what the alpha was interested in.  And he wasn’t going to take Dean bossing him around any longer.

Sam shoved Dean backwards and spread him out onto the desk, papers flying to the floor when he said, “I _need_ to taste you,” and went for Dean’s belt.  “I want to feel how wet I made you, want your slick on my tongue before its soaking my cock.”

“Jesus!” Dean cursed and arched his back, a shiver of pleasure rolling through his spine.  The alpha was making quick work of his pants and his boxers, he was completely at Sam's mercy as he clucked his tongue, in awe, “The mouth on you, alpha.”

A flare of arousal sparked anew when Dean used that word.  It also propelled Sam faster to rip away his clothing, not just down his knees but to his ankles.  Shit, Dean was now on display, a friggin feast for the wild alpha.

Instead of flipping him over and making him present right away, Sam surprised him.

He bent over and sucked the head of Dean’s cock while his fingers ventured between his legs, slick-coated and slippery.  Both sensations made the omega moan loud—accidentally too loud—and he needed to stifle his appreciation.  But, _fuck_!  The way Sam’s tongue swirled around his dick while his fingers teased around his needy hole?

It was too much teasing and not enough…action!

“Sam—” Dean had meant it to have a warning edge, but it came out as a pathetic plea, “Yer gonna have to suck a little harder, or finger-fuck me, or _something_ , because I’m about to lose it here!”

With a devious grin, Sam exchanged Dean’s erection for his mouth and kissed him urgently, sliding two fingers inside him at once.  Dean gasped against the alpha’s mouth and writhed, groaning, “Now that’s what I’m talking about!” raising his hips, trying to meet the fingers.  “How about we get down to business, Sammy?”

The name seemed to make the alpha preen, and he sucked a mark on Dean’s neck that had him thrashing.  You didn’t do that to an unmated omega, dammit!  It was _dangerous_ , it was perfect and not enough all at the same time—!

Fuck, Dean was gushing slick all over again, all over his mahogany desk.  This wasn’t exactly something he could ask the custodians to clean up either, this was an all-him mess, and an—

After another one of those phenomenal, take-your-breath-away kisses, Sam asked a heated, “How do you want it?  I can give it to you any way you can imagine, Dean.”  He nibbled the shell of the omega’s ear, still pumping his (now three) fingers in and out body, his voice downright filthy.  “I could fuck you sprawled out across the desk, just like this,” Sam grabbed Dean’s hips and hauled him towards the edge, as a point.

Dean was enrapture as Sam began unbuckling his own belt.  “I could sit in your office chair, let you ride me and fuck yourself on my cock.”  Oh, that was intriguing, and something that Dean very well may like one day.  But now—he wanted to give the power to Sam.  

Plus, he was distracted by Sam pulling out his fingers and sucking the slick off his digits.  “ _Fuck_ , you taste amazing,” he licked them clean, groaning he couldn’t get enough.  The alpha’s grin was devilish as he returned to unbuttoning and unzipping his khakis.  “I could lift you up, fuck you against your glass walls—the entire office would know that my cock was buried inside you, pounding into you so hard they could shatter.”

“No-not fair,” Dean finally said, “I get it, this is a scandalous quickie, but take yer fucking shirt off.  I need to see those muscles that could apparently ‘lift me up.’” Dean threw it out like a gauntlet, knowing it would appeal to an alpha.

There was a golden shine in his eye along with a growl when Sam ripped away his shirt and pulled his dick out of his pants at the same time.

“Ho-ly fuck,” Dean was breathless.

He didn’t know what to focus on because this alpha was perfection, right here, in front of him.  What he felt under his hand on his chest couldn’t do the real thing justice.  Sam was cut, ripped, without an ounce of fat on him.  And—once again—Dean’s hands had lied, because even when he’d wrapped his fist around Sam’s erection?

Shit, he had to have gotten it at a wrong angle, or something!  He had no idea the alpha was so long, the girth made him hungry and downright feral.  Sam’s posture changed again, like he was holding back, and it was probably because of Dean’s scent exploding with new desires.

Because he wanted him.  Fuck, did he _want_.

“I think,” Dean pushed off and onto his feet, “You like the original.  I think you’re gonna get off on the idea of bending me over my desk, fucking me from behind.”  He traced a single finger, a casual flirtatious touch along the length of Sam’s cock, making the alpha quiver.  Then, Dean ducked in and sucked a mark of his own, giving Sam a taste of his own medicine before he lewdly moaned, “I’m ready and waiting for that dick, Sammy, give it to me—”

While Dean was in the process of turning around, Sam was faster.  He maneuvered him with what appeared to be practiced ease (Dean would file that away for later) and pulled them far enough away that while Dean _would_ have purchase on the desk, he wouldn’t be laid out flat—having his cock trapped between his stomach and unforgiving wood.  How thoughtful.

Dean couldn’t keep the moans to himself when Sam rutted his dick between Dean’s thighs, between his ass cheeks, coating his cock with more slick than you’d find in a bottle of lube—fuck, it was everywhere!  Dean was surprised it hadn’t reached his kneecaps by now!

“C’mon, Sam, I’m waiting,” he slapped a hand down on the wood impatiently, and no sooner after did he feel the pressure of a thick, cock head breaching his rim.  “Yeeees—!” it was an elongated moan that refused to be muffled as Sam pushed into Dean’s body, stuffing him full.

Sam was panting, his grip on Dean’s hips rough, but the omega could tell he was trying to be as gentle as he could, keeping his inner animal at bay.  But Dean wasn’t breakable, in fact, the second he saw just how much alpha Sam had in him?  He craved every last bit of it.

“Never been stretched like this, Sam.  You’ve got some records to break, you know?”  Dean impishly lured him in, as Sam began rocking, the friction divine, “Now you g-gotta make me eat my words.  Make me say, ‘I’ve never been fucked like this,’ ‘I’ve never been so completely and utterly _wrecked_ like this,’ ‘I’ve never been so full of cum like this.’”

The snapping of Sam’s hips had accelerated—Dean having trouble, needing to force the words out—but disbelief and awe tinged the air coming from the alpha.  Sam draped himself over Dean, asking with nothing for sheer lust and amazement, “You’ll let me knot you?”  He picked up the pace and, in turn, the slap of his hips turned brutal—just how Dean had wanted.

“You’ll let me cum inside you?” Sam was gaining more steam, and his desire was palpable.  Hell, his knot was _already_ rubbing, beginning to catch on Dean’s rim.

With a shark like grin, Dean pushed backwards, meeting his rough thrusts and said, “Oh, you _will_  come inside me.  Gimme that knot, Sam.  Make me cum, just like this.”

He nodded avidly, and the moment his knot was worked inside Dean, the mere _knowledge_ was a turn on.  The spontaneity, the risk, Dean _didn't do this_ and it was intoxicating.  Sam was intoxicating.  Hell, there was no going back, and Dean was planning on taking advantage of this situation, using it for all it was worth.  He could hear Sam fighting for air, Dean could feel the acute pressure inside him and knew that Sam was close, probably closer—and the scenario was perfect.

“F- _fuck_ , Dean, I—” Sam stuttered out, his hands diving under the suit and caressing the omega’s skin in this combination of sweetness and fire.  And the way his nails raked down Dean’s back undeniably leaving reminders nearly pushed the omega over the edge.

But for now, Dean looked over his shoulder, swaying his hips and showing Sam the utter wanton desire when he ordered, “Knot me, Sam.  Wanna feel more of that huge cock, show me what you can do.”

The expression on Sam’s face, when they locked eyed, it was priceless and indescribable.  Like, lust-at-first-sight, dick-over-heels sexual chemistry that couldn’t be beaten.  Whatever was happening between them was insanity, and when Sam’s knot swelled, and that first load of cum rushed into Dean’s body neither of them could keep quiet.

Neither cared either.

The alpha was hesitant to continue rocking, clearly Sam was unsure about what Dean could and couldn’t handle.  That was why the omega had to do it for him.  Dean bucked backwards, ground down against Sam’s knot and made him gasp—that’s when Dean had an idea, something that sounded wonderful right now.

For as much as Sam had manhandled Dean, the omega gave it back however he could.  There wasn’t any grace to it as Dean shoved them back into his wide office chair, but this _had_  been on his mind since Sam brought it up.  And Dean decided now was the time to _take_.

The alpha slouched enough to plant his feet, to keep the chair from rolling, and so he could still thrust upward into Dean.  But Dean didn’t even need that.  No, he could spread his legs and reach the floor, even though they were tied together, and this was the perfect position to rock and grind, tug just enough on that knot to make Sam lose it.  Dean could tilt at _just_ the right angle and find his prostate.

When Dean nailed his sweet spot, Sam was already blowing another load inside him and that surge, directly against where Sam’s cockhead was already pounding his prostate?  Dean shouted out and doubled over, the most mind-blowing orgasm washing over him all at once.

There were also arms that surprisingly caught him.  Ones that pulled him backwards, against a warm chest and wrapped him in an embrace.  Then, lips on his neck that pressed sweet kisses while Dean’s insides were fit to burst in the most fantastic way.  He was still in a head daze when he realized that Sam was doing all these romantic after-glow things.

And, uh, should he be reciprocating?

“You’re amazing, Dean.  I didn’t see this coming and I don’t know what flipped the switch but,” Sam chuckled and used his height to his advantage, kissing his cheek, “I’m glad it did.”

Even from here, where Dean was being cuddled and Sam was sprawled out, amusement was lighting him up because he could see those damn shoes.  The gorgeous, designer shoes that led him to an even more gorgeous piece of alpha.

He wouldn’t say it.  Not until he got to know Sam a little bit better.

“Yeah, me too.”  Dean sighed and tried to crane his neck back up and over, “I like your happy scent.  Almost as much as I love that friggin perfect dick and the way you use it.  ‘Cause _goddamn_!”

“Did I live up to your expectations?”  Sam’s voice showed vulnerability, a new side to the man, and it made Dean wonder if the alpha’s next question on the list was going to be about making them a thing…

“Oh, did you ever,” the omega agreed, humming happily.  Dean took it upon himself, he broached the topic _before_ Sam would worry himself to death, “Pretty sure the entire floor knows just how my expectations were _exceeded_.  And if I remember right, you had a nice list of things you wanna do to me, so…” he left the innuendo out in the open, the alpha could pick it up and run with it or not.  It was his choice.

It didn’t matter to Dean one way or the other, but he did wanted to continue this stupefying sex.

“Seriously?” Sam perked up, voice full of hope.  “I mean, you’d want something?  With me?  After calling me a psychopath and blowing me off multiple times at work?”

“Hey!  Don’t push your luck!  Remember?  Switch flipped?  Don’t read into it too much or else yer gonna make me question if you’re—”

“I am.”  Very suddenly, Sam’s voice changed in timbre and he had this dead-seriousness to him.  While he continued to keep his arms around Dean, even going so far as to hold one, he instructed, “I’ll prove I’m not crazy, that I can be good to you, not just in bed.”  Before Dean could interject, Sam amended, “But _especially_ in bed,” which seemed to calm down the omega.

“Hell yeah.  This is gonna be fun.  I haven’t had a relationship, haven’t had time for one in—”

There was a loud knock at the door, and both of them froze.  While the lights were dim, they hadn’t been as quiet as they should have been.  There was also the little fact that Sam was buried, balls deep, inside Dean’s ass for the foreseeable future.  No one could answer that door right now.

“Mr. Smith!” A familiar voice called, and he hissed expletives under his breath—this was the _number one_ gossip across the entire board in the Sandover company.  “You left your briefcase in the parking garage!  You’re in there, right?”  Ruby’s voice told them everything they need to know.

Most importantly: she knew.

“Yep!  Finishing up some work, burning the midnight oil, I’ll grab it in a second,” Dean hollered back flatly.  When he didn’t see her shadow leave behind the heavily fogged doors or hear any rustling, he huffed and said, “Good night, Ruby!  Thank you!” with an unyielding tone.

“She’s sniffing the air,” Sam whispered into Dean’s ear, “She’ll know, she’ll—”

“Well, it’s a good thing you’re not just a quick fuck now, isn’t it?” he chuckled and decided to relax in Sam’s arms, actually enjoy the after glow.

Sam spoke in astonishment when he said, “You really are serious.”

“Wouldn’t say it if I wasn’t,  Kind of a man of my word around here.  You gotta be,” Dean closed his eyes, taken by the way this felt so…natural.  “You feel awesome.  Even in this lousy, poorly-planned position—you still made it work.  That’s dedication, right there,” he teased and Sam’s arms wrapped around him tighter.

“Imagine what I can do with a real bed.”

Well, _that_ thought certainly got Dean’s gears running all over again.  And he deliberately said, “Wanna take this back to your place after this?”

While Sam was pure enthusiasm and Dean was too... _maybe_ he had an ulterior motive.

Of course, he wanted to be fucked into a real mattress by this sex god of an alpha but he _also_ wanted to peek into Sam’s closet.    
  
Dean desperately needed to see what Sam's shoe collection was like...if these current designer duds (the ones Dean coveted and landed him a boyfriend in a weird twist of fate) were a fluke, or if the guy really _was_ friggin perfect.  Shit.  Now _Dean_ felt like the creeper he accused Sam of!

Still, this was important!  A pair of shoes (and, _ahem_ , size, for that matter) could tell you nearly all you need to know about a man.  It painted a damn good picture, and the omega had always had this... _thing_ about shoes.  There was also the fact that Dean may be completely captivated by the alpha he was currently knotted together with.  So what if he wanted a little more clarity in this picture?  That’s what boyfriends did.  


End file.
